Gossip Girl: Early days
by LonelyGirlWritesToPlease
Summary: Dan is nervous to meet The Serena Van Der Woodsen, but what will happen when he does? Will she feel the same way about him as he feels about her? Read and find out...
1. Chapter 1

**Gossip Girl: Early days**

Disclaimer: This is only a fan fiction, none of the characters or ideas are mines.

Hello guys, this is my first attempt at a fan fiction. Just to let you know the bold words are of gossip girl's narrative.

 **Morning Upper East Siders, it's time you learnt that sleeping through your holidays isn't going to drown your sorrows but that they will follow you until you wish you had a better distraction but surely you should know, you live in a city that never sleeps, that is its own consequence.**

Daniel Humphrey walked out of the coffee shop holding his usual hot chocolate and his side bag hitting his right leg, annoyingly. He had only a few minutes to get to Serena's house to give her back her book, she left in History class last week, before he would be late for school. He smiled as the inhaled fresh air, knowing that he would see Serena gave him butterflies in his stomach, he hoped his waffles would stay put.

Dan took the subway to Serena's house and ultimately there was an irrefutable change in atmosphere, no it wasn't the air or the morning birds he thought about, it was the transition from being amongst the mediocre middle classes that walked the streets in Brooklyn, to judgmental business people with overpriced possessions and definitely pride, in the Upper East Side. It was a wonder how Serena was so different living amongst them; she was lively and interesting, and exquisite. It was also a wonder why she would speak to him as surely Dan Humphrey from Brooklyn deserved even less attention than a rat living in a sewer or Serena's best friend Blair Waldorf thought anyway.

He stopped in front of the hotel gates: where Serena was staying whilst her mother finished renovating their old apartment. He composed himself and took a deep breathe making sure his tie was straight and he looked his best. He walked into the building and over to the reception.

"How can I help you." Asked the receptionist dully, almost as if out of habit as he didn't look very interested in helping Dan. But Dan asked him anyway.

"Hi I'm here to see Serena Van Der Woodsen."

"Well she just left, you can either wait for her over there or come back later." He said pointing to the empty chairs right ahead.

"Oh." Said Dan disappointed. He hoped that he would get to see Serena before school started and avoid her obnoxious and intolerable social fiasco's of friends , maybe he'd just come back tomorrow but earlier.

"Thank you, I'll just err… come back tomorrow."

The receptionist gave a fitting smile in response as he went back to his work. Then just as Dan turned to leave his breath got caught up his throat as he saw Serena walk into the hotel hurriedly. Her blonde curls were getting swept by her swift pace as she reached the elevator. She pressed the button and waited. Dan shook himself awake trying to function.

"She's here, go get her now." Said the receptionist nodded in Serena's direction.

Dan gulped trying to clear the lump in his throat as he hurriedly walked up to her but he could see that it was going to be too late as she walked into the elevator and Dan rushed in just in time. She seemed quite surprised with his sudden appearance.

"Hey, um… you probably don't remember me but you erm left this book in class last week and I thought you might need it." Dan held the book out in front of him.

"Oh um…thank you, you must be Dan Humphrey? From History?" she confirmed as she took the book without looking at it.

Dan wiped his sweaty palms on his leg as he chuckled nervously. "So you do remember me."

"Well you're not as invisible as you try to be."

"I don't try, I just happen to be."

"Well thank you anyway." Serena smiled gratefully making Dan's insides flutter a little. It was slightly awkward as now that he had given her book, it was only normal to leave but he was stuck in the lift with her.

"Well I would go now but I'm kind of stuck here with you…not that I don't want to…I err… are you not coming to school?" He asked trying to keep himself from stuttering, even though he could see she was dressed in her school uniform.

"No I just left…" she fumbled with the book Dan gave her until she read the cover. "I came back for this book, I thought I'd left it at home." She said surprised.

"Yeah so I brought it just in case you needed it for the test we have last period."

Dan looked into Serena's eyes as they glistened with the dim light of the elevator. Serena held his gaze not sure of why he was so nervous. Did he like her? She thought.

"So what chapters were we supposed to have looked at for the test? I've been over them just to be sure." She said innocently trying to make conversation.

Dan leaned over and showed her the chapters that were needed for the exam but she was too focused on studying Dan and his curly dark hair and how frequently his eyes fluttered when he was nervous. It was cute, she finally thought.

"But this chapter would be for the exam next week, so you should be okay with just that one." Dan said finally.

"Well maybe you can tell me over dinner tonight?"

Dan blinked. "Dinner?"

"Unless you don't want to of course."

"Oh no I would love to but would you really go out with me."

"Well I do really want to pass this history paper." She said earnestly.

Dan smiled, amazed at how Serena Van Der Woodsen asked him out to dinner.

Serena pressed the button for ground floor and finally they left the hotel.

"Hey you're going to school too right?" Serena asked Dan.

"Yeah."

"Let's share a cab."

"Oh no its fine I'll take the subway, I'm sure I won't be…" Dan checked his watch but realized he'd would be late. "I will be late. Let's go."

Serena and Dan sat quietly in the cab stealing glances at one another and nervously smiling until they reached school, they both parted. Serena walked up to the steps to meet with Blair and her minions whilst Dan made his way inside to the school library.

"Hey B." Serena greeted Blair with a warming huge.

"Hi S." Blair replied.

Blair was queen at Constance, she was never to be questioned but only answered to. She had quite a worthy reputation with her history of scheming surely it must pay of somewhere and it worked because Blair's desire for manipulation was as frequent as the one's need for nutrition, she could not and did not attempt to live without it. Blair was always wore the most expensive shoes to perfume, she always looked her finest, almost as if she had Chanel and Louis Vuitton on her speed dial, people would be more surprised to find out if she didn't.

Serena sat at the steps looking through her schedule.

"Oh I don't like having Chemistry on Monday mornings, it's stressful."

"Well at least it's only for a year, I had physics double period in the mornings for two years straight. Nothing can be more torturous." Just then a limo came to a stop outside the school gates, the door opened to reveal Chuck Bass. "Unless it's Chuck Bass of course."

"Morning ladies, it's always my pleasure to see you." Chuck said chivalrously, the corners of his mouth twisting into a mischievous yet mysterious smirk. Blair rolled her eyes whilst her minions giggled.

"Urrgh it's always a bad omen to see Chuck Bass. Go away Chuck I don't want to ruin my morning." Blair said with a wave of dismissal.

Just then everyone's phone beeped. Serena, Blair and Chuck took out their phones and saw an online post. Serena rolled her eyes, it was gossip girl.

 **Well upper east siders, rumour has it lonely boy isn't so lonely anymore. What is this we hear? He's going on a date The Serena Van Der Woodsen, dig deeper for evidence as this time we'll need more proof that this miracle has occurred.**

"Who is he?" Blair looking at the picture gossip girl had posted.

"Daniel Humphrey, I see you've decided to get dirty in Brooklyn, you'll feel there's always a different rush of adrenaline with using something that hasn't been used or competed with in this matter-"

Chuck hadn't finished when Serena shoved him out of the way.

"Gross." Serena said frustrated. "But yes, we are going on a date."

Blair didn't even respond with the disgust written on her face.

"I'll let you know how it goes B." Serena squeaked with excitement.

 **I hope you liked what I've written so far, leave a review to let me know what you think :))**


	2. Chapter 2

**Gossip girl**

As Serena walked off Blair got up and dragged Chuck to the side.

"What are we going to do about this?" She asked.

"About what?"

"About Serena dating this new guy, I mean who even is he? Come on we know Serena and the mistakes she makes with the guys she 'dates', we have to save her."

Chuck narrowed his eyes thinking. "He's from Brooklyn, he's nobody, she'll be over him when she sees the filth on the streets he lives. We, on the other hand, can make things more interesting in another way." Chuck said lightly brushing his fingers across Blair's cheek. Blair shoved his hand away.

"Focus, she's my best friend, I won't let her do anything she regrets."

"You mean like the time you gave her so many tequila shots that she almost…well…do I even need to say."

"Don't act like you didn't pay for them." Blair murmured as she glared at Chuck.

Chuck studied her and finally came to the conclusion that she was serious.

"Fine, what do you suggest?" He said.

"Well we can always try the classic, they are on their date and then suddenly Dan 'girlfriend' turns up. Although it would be hard to believe he has one but it should end things."

"Hmm… that's too boring, not worth my time." Chuck thought. "Or how about…" Chuck whispered his idea into Blair's ear, and watched as her eyes began to sparkle with excitement.

"Not bad Bass."

"See you after school." Chuck said as he turned around.

"Where are you going?"

"I'm not feeling school anymore." Chuck replied and like what he did most of time, he disappeared, after all he was Chuck Bass but where did he go? And what did he do? These questions only Bass can answer.

It was six in the evening and Blair was looking for Chuck, but he wasn't at home. She dialled Serena's number.

"Hi S have you seen Chuck?"

"No actually I haven't. Why is everything okay?"

"Err…" Blair thought, how would she answer that? Chuck and her weren't exactly the best of friends and in fact they loathed the mere presence of one another.

"Yeah I just had to give him something, it's okay if you don't know."

"Have you tried the Palace Bar?"

"No I haven't but I will right away."

"I have to go and get ready for my date by the way."

"Okay bye." Blair hung up not evening wishing her luck but she saw no point when she was going to be the destroying any she had in the first place.

Blair made her way to the Chuck's hotel bar. She stood by the entrance and her eyes searched the bar until they found a boy hunched over an empty drink. The bartender took his glass and refilled it with scotch. He handed the drink to Chuck. Chuck looked at the glass and then at the bartender.

"Bit more, I own this place for God's sake." He slurred his words. The bartender eyed him with annoyance whilst pouring some more scotch into his glass until it was full. Chuck took it and placed it directly under his gaze, staring hard into the liquid, scrutinising it, trying to see what it was that made him drink so much. Was it how it calmed him when he couldn't control his feelings of being abandoned by his father? Or was it that each time he wanted someone around him, just a friend sometimes, his drink would easily provide with him better company. The drink didn't let him feel like he was letting someone down whether it was his father or his friends. But of course it was only a guess Blair was making, she couldn't be sure of how dark or lonely his thoughts were, no one could.

It pained Blair to see him sitting alone, even whilst knowing he had friends, why did he not give anyone the chance to love him, why did he not give Blair the chance to love him. Blair shook her head to clear her thoughts; she wasn't here for that, she was here to save her best friend from making another disastrous boyfriend and being hurt. She was over Chuck and he was no longer her problem. She held her head high and walked up to him.

"Chuck we're late." She said.

Chuck grimaced and slightly turned his head to Blair.

"You don't need me, you can do it on your own."

"That's true, but it wasn't my idea, so I'm not going to take the entire responsibility if when Serena finds, which she will, as it isn't exactly flawless." Blair crossed her arms across her chest and pouted.

"I'm not feeling it anymore. Stop wasting my time." Chuck said his lips barely moving.

"Chuck you can't do this, it's not about us, it's about Serena."

Chuck continued to stare morbidly ahead, choosing not to reply.

Blair huffed and slowly walked away, hoping he would stop her but just like always he never did and she continued to walk away. Chuck titled his head in Blair direction and closed his eyes, when will she learn that I can never make her happy? He thought frustrated.

Blair took out her phone and dialled Dorota's number.

"Get ready because things are going to get messy."

 **We hear first kisses are memorable but first love unforgettable. Does Queen B think she'll ever get rid of Bass? Or is she still secretly waiting for his feelings to become mutual, whichever it is, you'd better hurry Bass or Queen B will act.**


	3. Chapter 3

Serena arrived at the address that Dan had texted her and stood waiting. She was outside one of the most expensive restaurants in Manhattan. It was weird, Serena knew that Dan Humphrey was from Brooklyn and also meant he wouldn't be so well off, she hoped he knew what he was doing. Just as she rubbed her arms from the cold, she spotted Dan coming down the street, nervously feeling his blazer as though it were a foreign material to his body.

Serena sighed as she shook her head mentally, knowing he was making too much effort for this date. Expensive clothes and expensive restaurant was simply not going to do.

"Hey." Dan greeted nervously.

"Hi." Serena replied.

"So shall we go inside?" Dan asked.

"Umm…" Serena hesitated not sure how to tell him, she didn't want to eat at a restaurant, she looked around nervously at the shop.

"What's wrong?" Dan asked softly.

"Nothing its just that…" She looked into the shop and saw it's golden classical theme and even though it was pretty, she didn't want to spend her evening in there. Then suddenly she spotted Blair sitting one of the back chairs, peeking over the menu, as she used it to hide her face, as Blair saw that Serena was looking her way, she ducked. Serena pursed her lips knowing exactly what Blair was doing.

"Is everything okay?" Dan asked again, this time more curious.

"No you know what let's go somewhere I haven't been before."

"Oh, I thought you would like it here." Dan said.

"Oh no, it's not that I don't, it's just I've been here too many times, and I know too many people here." She mumbled the last part to herself.

"Okay so where do you want to go?" Dan asked.

"Somewhere where I haven't been before, surprise me." She said with a smile.

"Somewhere where you haven't been?" Dan asked as if it were a challenge.

"Somewhere where I haven't been." Serena replied.

"Okay then I won't be needing this." Dan took of his blazer and placed it around Serena's shoulders, as he realised that she was cold. Serena held onto the fabric gratefully.

"Thanks." She smiled.

"Come on let's go then."

"Where to?" Serena asked.

"Somewhere where you've never been." Dan said. Serena lightly chuckled and watched Dan as she realised how much his dark navy shirt suited him, it complimented his body and brought out the colour of his eyes. Dark and Deep black. A colour she avoided due to its plainness and memories of her past but now she was starting to like it again. She was starting to see it in a different way.

Blair saw Serena walk off with Dan. She must've seen her, Blair thought, annoyed.

"Would you like some more Champagne?" The waiter asked Blair in a French accent.

"No thank you, that'll be it."

"Are you sure, you're food hasn't arrived yet."

"Did you not hear me, or do they not say no in France, I'm leaving." Blair placed the money for the champagne he had on the table and left abruptly, leaving the waiter feeling ashamed.

Blair got hold off a cab and sat in.

"Where to?" The cab driver asked. Blair thought for a moment, she didn't feel like going home and Chuck was drunk so she couldn't visit him but she could visit Nate.

"75 Rutcherfield Avenue please."

She arrived at his house after a few minutes and knocked on the door. Nate opened it within seconds.

"Hey." He said. "Come on in."

Blair walked in.

"Okay so Serena is on a date with this loser and Chuck like always is drunk, I don't know why but I'm worrying about him." She said in a small voice.

"Okay calm down and sit, let me get you something to drink."

Blair took a seat and took out her phone, she saw that she had a message from Serena.

 **Serena: Wat were u doin at the restaurant?**

 **Blair: Trying to make you see that you're making a mistake. Run away from him. It's not too late.**

 **Serena: It's my choice who I want to date, not urs.**

 **Blair: Suit yourself.**

"Here you are." Nate handed her a glass of water. Blair took a sip and put it down.

"I'm worrying about Chuck." Blair started. "I know that he's always been like that for a long time, but it has got to stop, he's destroying himself and we can't let that happen."

"Yeah I've tried talking to him but he doesn't listen. There's not much we can do anymore."

"I feel like he's been worse since we broke up last month."

"Hmm… yeah."

They went silent as they thought for a moment about what they could do.

"So who did you say Serena was dating." Nate curiously.

"Urghh, Dan Humphrey."

Nate raised his eyebrow. "Who."

"The only kid that takes the Metro to school… I don't know lives in Brooklyn."

"Oh." Nate said thoughtfully nodding.

"Yeah."

"Why? Still not over her?" Blair asked tilting her head.

"No just asking, so now I know she's moved on. Didn't take her long, we broke up just two weeks ago."

"Well I was going to break them up today if that makes you feel any better but then Serena saw me at the restaurant and went to away."

"Well if she really likes him, you should let them be." Nate said. Blair could hear the sadness in Nate's voice.

"Maybe but Serena happens to like every boy on her first date." The she stood up. "I should go but try talking some sense into Chuck one more time and let me know what he says."

"You really care about him, don't you?" Nate asked.

"I do." Blair said simply, sighing as she wished he did too and then she left.

 **Violets are red and roses are blue, B has united with A, will C listen to these two. We hear Queen B has mission and surprisingly it's not expanding her kingdom. Will this new quest for love be worth it, only B will know and only C can tell. Upper East Siders hold onto your seats as we are going to see two explosives meet.**


	4. Chapter 4

**Gossip Girl – Chapter 4**

Dan stood by the railing, as he moved Serena's hair out of her face, slowly memorising all her features, slowly memorising all of her. She was beautiful, he breathed. Serena suddenly looked away smiling anxiously.

"Was it something I did?" Dan asked suddenly feeling worried that he did something wrong.

"No no it's nothing you did, it's the way you look at me." She whispered.

"And do you like it?" Dan asked leaning in.

Serena looked at Dan and thought how different he was, each word he said was genuine, she didn't have to worry about whether he was lying and she couldn't say that about many people. It was so simple being with him, time was flying too fast in her opinion, so far they had Brooklyn's famous burger and fries and it was so much fun. There were no rules on how to eat or how much to eat or even what to say and what not to say. She laughed as though being with a friend she felt like she knew for a very long time. But every time he looked at her, listened to her and even said her name, her heart would skip a beat. She spent most of her time being lost in his dark, deep eyes trying to decipher his expressions every time he spoke about his favourite books, films and tv stars. She had the feeling that some things he genuinely like and others he just pretended to impress but nevertheless she thought it was cute. There never had been anyone who'd cared so much about her opinion.

"Could you move along, please?" Said the guy standing behind them in the Que. Dan had decided to take her to her dad's concert after they'd finished eating, it would be two places she had never been to.

Serena and Dan shuffled up slightly, it was just another few minutes until the concert would begin but Dan began to get worried that Serena would get bored.

"I think I know a quicker way to get in."

"It's okay, the doors are opening in a couple of minutes."

"C'mon, my dad is the singer we can get in through the back way and for free, why didn't I think of that before?" Dan mentally slapped himself, he definitely looked stupid now.

Dan lead the way to the back and knocked on the door, one of the crew members opened it and let them in once Dan explained who he was. They went in, through the dressing rooms and then to back stage. Dan's dad, Rufus Humphrey, stood waiting for his show to begin. He took deep breathes as he peeked at the crowd through the side of the back stage.

"You'll be fine dad." Rufus spun around, and nervously laughed.

"I knew you would come and I see you brought your date too."

"Yeah dad, meet Serena, Serena my dad."

"Hello." Serena greeted Rufus with a smile.

"Hello, so are you..Serena… Serena Van Der Woodsen?"

"Yes I am."

"Oh you look even more beautiful than in pictures Dan has of you."

Dan's face went red with embarrassment. She wondered which pictures he had, instantly and how she looked in them.

"Dad." Dan moaned.

"Well kids enjoy the show." Rufus said.

Dan lead Serena down the couple of steps and into the crowd, he took her hand in his as he lead them to the front row. There were hundreds of people behind us, eagerly waiting for the show begin and then minutes passed and the time as the presenter, Cindy Showers, came on stage to begin the concert.

"Ladies and Gentlemen, I give you Rufus Humphrey." Rufus came on stage with his guitar and the crowd erupted into huge excited roars. Rufus' expression remained calm, hiding his nerves as even though he had performed the same songs so many times, each time was different, each time had different people and different experiences that he used to put meaning and emotion into his written words, he hoped each time the words would suffice and touch the soul of each member in the crowd.

The instance Rufus struck the strings of his guitar, he had swept the crowd senselessly of their feet and Serena hopelessly joined in. Dan watched her as she was so lively.

"Your dad has a really good voice, I love the songs." She commented over the noise.

"Thank you." Dan replied although he wasn't so sure she'd heard over the noise.

The elevator opened and Chuck fell out, hitting a vase over, causing it to break into pieces on the floor. Bart, Chuck's dad, turned around as he knew it could be no other than his drunk son Chuck, it was his usual time to stroll in after all. Bart walked over to Chuck, who struggled on the floor and stared at him with disappointment, unable to find the right words to express how he thought the child struggling on the floor could be helped.

He couldn't see clearly but he made out a vague figure of his dad. "Go away, I don't need your help." Chuck slurred on his words.

"I wasn't going to help you." The Bart crouch down to Chuck and whispered. "You can't be helped." Chuck massaged his temple, unsure of how to respond to those words, or even unsure of how much truth they held, probably a lot since he was in this state for every night for the last couple of months.

Bart walked away, leaving Chuck to help himself, like he always did.

Chucks head hurt to even think of another way to get his body to work but he heard the bell ring for the lift. They had a visitor, now he would have to get up.

"Are you okay?" Came a worried Blair's voice.

Chuck grunted in response.

She tried to help him up but failed. Eventually she called Chuck's personal Butler and he helped him to bed. Blair took off his shoes and pulled his duvet higher above his waist. She was about to leave until Chuck held onto her arm and pulled her closer. She waited a heartbeat for him to speak.

"Stay away from me." Chuck managed and with that he fell supposedly asleep or what Blair thought unconscious. A tear fell down Blair cheek, as she saw him in the helpless state he was in but then she was angry with herself, what was the point of letting tears out for a person that was never going to be there to wipe them, she thought. She brushed it off.

"Goodbye Chuck, I made some good memories with you." And with that Blair left the apartment swearing to herself that she would never return.

 **A swear and an oath hold the same value as neither can be taken back. Surely Queen B was taught that but it doesn't matter if she wasn't as we'll now see her learn it the hard way. It's time Upper East Siders to replace you popcorns with something darkly sweeter as B will try to replace her memories of Chuck with some equally or maybe even greater, but with who and where? I know this secret but I'll never tell after all, that's who I am.**

 **XOXO Gossip Girl.**

 **Hii everyone, thank you so much for your comments, they are so supportive. I am going to put more of Blair and Chuck's story into the fanfic now but keep reviewing to let me know what you think and like to read more of and also don't forget to Fav if you like it :)) teehee.**


	5. Chapter 5

**Gossip Girl – Chapter 5**

 **I sincerely apologize to all Derena fans for this chapter as it is about Blair and Chuck, I wrote this before your requests and promise to write more about Dan and Serena in the next one.**

 **I have also changed a lot of it, so it is worth reading again.**

Chuck woke up with a throbbing headache. He flicked his eyes open and instantly closed them, the warm sunlight felt poisonous to his eyes.

"Hey man wake up. I have something to tell you." Came Nate's monotone voice.

Chuck grunted in response. "Close the curtains." He barely managed.

Nate set down the special smoothie they drank to cure their hangovers, on the able beside Chuck's bed.

"Seriously, I'm not going to lie. Get up."

Reluctantly Chuck dragged himself out of bed and took a sip of the smoothie. He then went for a shower. Nate waited on his return a couple of minutes later.

"What is it?" Chuck asked, massaging his temples as he took a huge gulp of smoothie.

"Blair's gone."

"What do you mean?" Chuck said trying to repeat Nate's words in his head.

"I mean that it's been a week and no one knows where she is, she was last spotted at your house, last week."

"Yeah she was here." Chuck said whilst thinking about where she could go. "I'll need a couple of more hours, I can't think clearly."

"Fine, text me and I'll come by." Nate said and then he left. Leaving Chuck pondering what Blair had said to him last time, he couldn't remember anything other than her worrying about him. Chuck grazed the bottom of his lip with the tip of his finger, where could she have gone? He thought but his mind was blank.

He reached over to his table for his phone and speed dialled Arthur, his dad's personal investigator. "Hey I need a favour." Chuck began.

A couple of hours later, Nate came by to Chuck's despite not having received a message, he knew he wouldn't get one.

"Chuck?" Nate said as he walked in.

"In here." Came Chuck's voice.

Nate went into his room and saw Chuck sat on his bed, leaning on the frame and with his eyes narrowed and fixated on a blank spot as though thinking hard about something, well that's what he looked like he was doing. No one could tell for certain what went on in his mind.

"So did you find out where Blair is?"

"Not only did I find out where she is, I also found out who she's with." Chuck said.

"And?" Nate asked.

"She's with Carter Baizen, in Germany."

"Carter Baizen, in Germany?" Nate asked. He was not expecting this at all.

"Yeah, she knows." Chuck said.

"She knows what?" Nate asked, feeling like he knew nothing.

Chuck looked up at Nate and took a deep breathe. Whatever he was going to say next, Nate would not like it.

"Last fall, just before Blair and I broke up, I went to Europe to help Serena. Remember that? She went missing for a long time."

Nate nodded hurriedly trying to see where this was going.

"Well it turns out that there was this guy that she ended up marrying, can't remember his name much but the guy had her sign this contract that said she was handing her half of the property that Lilly had for her until she turned eighteen. And so to get her out of that mess I had to pay the guy with money. A lot of money."

Nate gasped. "What? Why did nobody tell me?"

"It happened all too fast and you know with Serena things get messy easily."

"How much money was it?"

"A couple of millions." Chuck whispered.

"No! How did you pay that much."

Chuck dropped his head into his hands.

"I sold one of my dad's properties. The only one that gave me that much money was the Real Estate. You know the first property that my dad ever brought. The one that started off his career. I forged his signature and sold it."

Nate jaw dropped open. "What? How? When? You did that?"

"Does he know?"

"Yeah it's obvious he's found out. He's cut all ties with me. Just letting me stay here, so I don't give him bad press lying on the streets."

Nate raised his eyebrow. "Chuck! Oh my God! That is bad."

"I'm the billionaires son that couldn't handle the pressure of being rich." Chuck lowered his gaze at his hands. "Just a few days away from being kicked out of here."

"Do Serena and Blair know this? But then why did Blair break up with you?" Nate asked, a million questions had come to his mind and he felt betrayed for not knowing anything.

"No, no-one other than my dad knows. Serena doesn't know how much money I gave or even where I got it from. I-I" Chuck felt his voice go dry whilst talking about why he broke up with Blair. "I broke up with Blair because my dad's broken all ties with me, meaning that I have no money, property, nothing. I have nothing. Nothing for her or myself."

"Chuck but that's not…" Nate trailed off not knowing how to phrase what he wanted to say.

"Not what? We both know that without money we're nothing. We're just like everyone else. Blair was something real, I didn't want to give her a false idea of a future we would have together. I have no future." Chuck said through his teeth, feeling broken. For the first time Chuck actually hated who he was.

"If Blair was something real, then money wouldn't have mattered." Nate offered but mentally slapped himself wondering whether that was the best he could offer.

"Nathaniel it's money. We need it not only to survive but to live."

"Blair has money."

"But I have nothing." Chuck stood up.

"You have your name. You can start a career with that in a few years."

"My wonderful Father is getting it changed."

Chuck rubbed huis temples feeling the urge to drink his pain away. Nate and Chuck stayed quiet for a moment.

"So you've been drinking to rid of the problem. Dude that's no way to deal with it."

"No drinking hasn't helped me get rid of the problem, it's helped me stop thinking of the mess I am in."

"So what now?"

"That's a good question to what I have no answer to." Chuck said. "I don't know."

"You need to tell Serena where you got the money, she has some money she could give to you and then from that you can start a business or some sort of career."

"I don't know."

"It is a complete contradiction to simply say that you had fun with Dan Humphrey and then in Brooklyn, it's a tacky place, we can't be associated with him or anything from there." Blair said as she went through the selection of clothes.

"No Blair, he was really nice and charming."

"Humphrey and Charming? Really? Think carefully S, we didn't even know the guy until you left your book in history class and he chased you into the lift, he sounds like a creep."

"How does this one look?" Serena said as she pulled out a purple dress, with silver sequences. "You don't get it, he's different, he makes me feel different."

"That's what they all are. Different and then they get what they want and they become indifferent and just as rude and brainless as all the other men. I mean look at Chuck, one day he tells me something he hasn't uttered to another woman and the next day he leaves me to go to Europe for no reason, and also try the same dress but in red."

"He still hasn't come around." Serena asked as she looked at the red dress and realised Blair was right, the red one appeared to give a more confident and classy appeal.

"No and I'm trying to forget him and everything to do with him but in order to do that I need to know the reason he left me and then I promise after that, there will be no more Blair and Chuck, in fact the name Chuck shall be forever erased from my life, no one shall speak of him."

"You don't mean that."

"I do. Why do you think, I'm here with Carter Bayson."

"Wait what? Carter is here?!" Serena asked shocked. "You know Carter is a dangerous person."

"He's the only one that came to my mind when saw Chuck in his completely destroyed state; anyway let's talk about something else. What are you plans for Christmas?"

 **Tis the season to be honest B. The jingle bells will chime as soon as you find your present but be known that it won't be as easy, maybe secret Santa has another present than what you had in mind because we know that all those who snoop around find nasty surprises which then can't be unknown. Be careful with finding C's secrets B, you don't want to step onto a needle you've already seen coming in your path.**

 **Just to let you guys know I will be having more of Derena, just keep reading and you'll find out. Teehee :))**


	6. Chapter 6

**Gossip Girl: Chapter 6**

Dan stared at his laptop screen point blanc, he was having this moment every writer would eventually experience at some point during their career, where they couldn't decide which words to use to describe something. Dan always had the feared he wouldn't be able to convey his experience or emotion with words that could make the readers understand exactly what it was he felt. He was entering a competition for the New Yorker and really hoped that he would win it because part of the prize was to get his piece published in the New Yorker Writer's Magazine. But in order to win Dan had been trying to find the perfect opening line for hours since he sat down. In fact he was sure in a couple of minutes he was going to reach the point where he wouldn't care how he started it off as long as he started it off.

"Stuck somewhere son?" Rufus asked as he walked into the loft. Rufus walked in to get a file from his table. He shuffled through a pile of papers, looking for his document intently.

"Err…Yeah, I don't know how to start."

"Start? You've been sat there since I left for work."

"I know but I'm about to write something special and I'm nervous. I want it to be good. I want to do justice to my experience. Have you ever written a song about something special and wanted it to be the best thing you write, ever."

"You sound like you're falling for someone?" Rufus cocked his head in Dan's direction.

Dan chuckled nervously. "I don't know. I don't know what it's supposed to feel like."

"Well she definitely just came to your mind. I'm guessing this is about Serena."

For a moment Dan stayed quiet. "It is." He admitted.

"I can understand, The Van Derson Women." Rufus said as he sighed.

"Van Derson Women?" Dan asked curiously.

"No nothing just take a deep breath and start with what came to you heart the moment you saw her and then the characters will write the scene for you." Rufus advised.

Dan thought about it. What was the first thing that came to his mind when he saw Serena? God that she's beautiful, she's breath-taking, she's the girl he wanted to be with forever.

"Just don't make it a cliché." Rufus said as if he'd read Dan's thoughts.

"Okay I won't. Thanks dad."

"Anytime. I have to get back now, I'll see you and Jenny for dinner tonight."

"Okay bye." Then Rufus left, leaving Dan alone with his thoughts once again.

Dan starred at the empty page on the word document and rubbed his fingers together as he set his finger on the keyboard and began to write…

Serena had just arrived home from meeting Blair and Germany. She set her things down in her room and lay in her bed feeling jet lagged. She took out her phone and expected a phone call or even a message from Dan but there was nothing. She suddenly felt emptiness; she wanted to talk to him not about Blair but just talk. Maybe she should call him? Or even better maybe she should give him a surprise visit. She had stayed in Germany for a week and so she hadn't seen him for so long.

Serena grabbed her jacket and left her apartment.

"Taxi." She waved at a cab as it came to a stop in front of her. She opened the door and sat in.

"To Brooklyn please."

Dan had begun writing and hadn't stopped since. He had managed to write three pages so far and he couldn't stop writing all the metaphors and similes that described his date with Serena, he just didn't want it to be one short from the reading imagining his date and how happy he was.

Then Dan heard a knock on the door.

"Jenny could you get that please." Dan shouted to Jenny who was in his room.

"Urgh okay." She said walking out of her bedroom and opening the door. Dan heard Jenny giggle but didn't think much of it. It might've been one of her friends from school. Dan concentrated on his writing piece, it was going so well.

Suddenly he felt two arms snake around his neck and smelt a very sophisticated, expensive fragrance. He must've been writing a lot about Serena, he thought, he could feel and even smell her now.

"You're writing about me?" Serena asked.

Dan turned to look surprised to see Serena actually standing behind him. He jumped up.

"Serena oh um…hi." He managed through his shock. They had been dating three weeks but he still couldn't hadn't learnt how breathe around her.

"I'm sorry did I scare you?" Serena asked seeing him suddenly alarmed. He could hear Jenny laughing in the kitchen, wanting to silence her desperately.

"No no you didn't I just didn't expect you, you know but umm…how was your trip to Germany." Dan moved over to give Serena a huge hug.

"It was good just Blair and stuff."

"Good." Dan replied nervously. "Why don't you sit down, can I get you something to eat or drink?"

"I wouldn't mind." Serena said taking Dan's seat and sitting in front of his laptop. Dan went to the kitchen to find something to eat or drink. He hadn't known Serena was going to come down tonight otherwise he would definitely have worn other clothes and straightened his hair.

Serena looked curiously at Dan's laptop knowing that when she hugged him from the back he was writing something and if she hadn't been mistaken she also saw her name on it. Slowly she pulled up the laptop screen and scrolled to the top of the page. It read: **A dream come true.**

 **When I saw the stars, they twinkled like they did on any other day but today I saw a mini sparkle about which I began to fear I might've missed if it wasn't for me being so deeply in love. The sky was as dark as it could ever be and my heart beated faster and felt lighter as I thought about the girl I had met just a couple of weeks ago. Who knew it was so easy to fall in love. They said that only happened if it was real, was this real? I began to ponder why this was so different? Why she managed to have gotten falling so hard? Yes I had dated before but this seemed nothing like it. This was a story of a boy whose dream had come true but not in the way he expected nevertheless he was happy because he had her-**

Then Dan took the laptop away and put the screen down, he laughed nervously.

"You don't need to read that." He said.

"But why? It was so good, it was about me." Serena whispered as it dawned on her that it was about her. "Please let me read it." she asked.

"That is a draft; it cannot even be spoken of until it is complete." Dan said, he got really nervous when anyone read his drafts, he was conscious of too many mistakes or even ideas that seemed good at the time but when he edited it later he realised they weren't so good or in this case it would be too cheesy.

"Please Dan." Serena pouted making it harder for Dan to stay firm in his decision. She looked at him earnestly.

"No, I'm so sorry but you can as soon as I finish." He said. Serena took the glass of juice from the table.

"Also how about we go out to eat instead?" Dan asked. "There's nothing much at home." Plus he had to get her away from the laptop. Serena looked at laptop for a good few seconds before she realised she had to give up and wait.

"Fine. Also I wanted to invite you to meet my friends at the Grand ball next week. You're coming right?"

"Are you asking me to come with you?" Dan asked flirtatiously.

"I might be."

"Well then how I could I ever say no." Dan beamed at her.

 **Well well we hear champagne will be served and roses will be exchanged at the Upper East Ball. Be careful S will your relationship survive the thorns or will it merely suffer the consequences of where you hopelessly come from. You'll see lonely boy won't see eye to eye on many things we that will happen. I would say good luck but I already know what will happen but I'll never tell. You know you love me xoxo gossip girl.**


	7. Chapter 7

**Gossip Girl: Chapter 7**

"Jenny! You need to help me!" Dan said impatiently. He couldn't decide whether to wear a bow tie or a normal tie. Should it be black or red? The green one didn't look so Upper East Side material. Dan had just hired a suit, from one of a high brands. His main concern that evening was getting the suit home in one piece because one thing he couldn't afford was repairing it.  
"What is it?" Jenny asked.  
"This one or this one?" Dan asked.  
"Well what colour is she wearing?" Jenny asked.  
"Last time I spoke to her, I think she said blue? Maybe."  
Jenny huffed. "Just wear the black bow tie, it's the safer option." Jenny shook her head, she had never seen her brother this fussed about how he looked. She understood that it was the Grand Ball but Dan was never interested in high society events. He used to call them masquerades, an excuse to flaunt money and wealth with the obvious that went with that, power but all in the name of tradition. Dan used to say that if everyone human in the ballroom was humble then there would be no one there. And now he was going in, she hoped he would come back out the same.  
"Alright, how do I look?" Dan asked finally.  
"I think you look great, now go!"  
Dan was meeting Serena outside the ball and it seemed that Serena was five minutes late, but he wait patiently. Then he saw her limo stopping outside of the Grand Ball, the door opened and out came his princess. She wore a light pink dress, with such minimal make up but yet she looked flawless. The moment her eyes found his in the crowd, Dan forgot everything and everyone. The sounds of the paparazzi had died down and the people moving past Dan were no longer bothering him. He wished in that moment he could stand and stare at her forever.  
Serena stepped out of the limo, hoping to balance fine on her heels. She searched the crowd for Dan but when she found him he was already staring at her. That gave her stomach butterflies. She smiled as she blushed. Dan himself looked really good, they say wearing a suit makes anyone look good but Dan looked really handsome. It was different from his messy writer look. His hair was curly and he wore a bow tie, at which Serena smiled, she liked bow ties.  
Serena walked up to him.  
"Sorry I'm late." She said. She locked her arm in his. "Shall we?"  
Dan didn't realise when he starting walking again but he leaned into Serena and whispered. "You look beautiful."  
"You don't look too bad yourself." She said playfully.  
They then entered the Grand Hall. It was truly exquisite and classy. The theme had been beige and cream, with high mighty chandeliers that hung the hall. There was a harp, and a piano being played in the corner, something classical that had every note resonating through the hall. Everyone was looking good, people holding champagne glasses looking exceptionally happy, exceptionally successful. Dan could smell the delicious appetisers, that were made with such perfection. Dan didn't even bother asking what they were called, since they'd be named after some French Chef or Greek.  
Just then Dan heard Serena squeak. He turned around to see that she was greeting Blair.  
"Blair meet Dan, Dan meet my best friend Blair."  
"Hi, nice meeting you."  
Blair looked Dan head to toe and grimaced. "Wish I could say the same."  
Well Dan wasn't expecting warm hugs and kisses but Blair was really intimidating. Like most others Blair didn't even bother putting on a facade and hiding her arrogance. Dan wasn't sure whether to respect the honesty or resent it.  
"Blair be nice." Serena said.  
Blair put a hand on her hip and pouted.  
"Not even going to try."

Just then Nate appeared.

"Serena you made it?" Nate greeted her.

"Nate meet Dan, Dan this is my friend Nate." Dan held his hand out to Nate who didn't shake it but looked around awkwardly.

"Dan, would you mind getting me a drink." Dan nodded thankful for an excuse to be somewhere else and not with Serena's stuck up friends. Dan could feel his ears have gone red from embarrassment.

"You need to be nicer." Serena said to Blair and Nate.

They both rolled their eyes.

"What?" Serena asked. "I like him."

"You always like them." Blair said.

"He's different."

"Whatever." Blair wavered Serena. "Have you guys seen Chuck?"

"I was going to ask you the same question?"

Suddenly Blair looked away unable to veil her sadness, if she didn't say how much it pained her, her said it all.

"You should speak to him." Nate said earnestly to Blair.

"I already have." Blair said.

"No you need to speak to him when he's sober." Nate said.

"Why?" Blair turned to Nate, looking at him curiously as if he knew something she didn't.

Dan walked over to the table with food and then appeared a waiter, holding champagne glasses.

"Hey are you okay?" She asked.

Dan's throat was dry and his face was probably red.

"Yeah I just need one of these." He took a champagne glass and threw the liquid down his throat. It wasn't his smartest idea. His throat burned from the fizz but he's head felt lighter.

"Careful." The waiter said wearily. "You're supposed to sip these. Not even drink a whole glass during the evening."

"I can't be sober for this." Dan said almost to himself.

"You kind of have to be. Unless you want to be the laughing stock of this year. Which is impossible because William Wetherbyern took that title when he insulted his father while he was drunk."

"You saw that?" Dan asked her.

"I've seen a lot more than happens around here." She replied.

"My name is Dan and yours is?"

"Sorry I didn't introduce myself. My name is Darena."

"Nice name." Dan commented. Darena had black hair and brown eyes, she was a waiter at this party, so she was dressed formerly. She looked about the same age as Dan.

"You're not from here?" Dan asked.

"I'm from Brooklyn. If I was from here, I'd be in a dress holding a champagne in my hand not serving them."

"Right now now I wish I was serving champagne." Dan said. Darena laughed.

"So you're not an Upper East Sider either?"

"No I'm from Brooklyn too. I'm her date." Dan said pointing to Serena, who was laughing flawlessly.

"Oh she is pretty."

"She is, isn't she." Dan said. "I should get back to her."

 **What is this we hear, Upper East Siders, we have intruders being invited to the ball. Making friends with foes and did Cinderella get invited or did she play politics to get to the throne? Cindy left her shoe, what will lonely boy leave in the hope of another date. That is one secret I will never tell. XOXO Gossip Girl.**

 **Hi Guys sorry for the late update! I hope you like this new chapter. Darena is a new character that is going to make things interesting. Leave a review and tell me what you think. Teehee :))**


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